Rapid stereoselective access to the tetracyclic core of puupehenone and related sponge metabolites using metal-free radical cyclisations of cyclohexenyl-substituted 3-bromochroman-4-ones

Tetrahedron Letters

Volumn 49, Issue 26, 2008, Pages 4156-4159

  Pritchard, Robin G ^a   Sheldrake, Helen M ^a   Taylor, Isobel Z ^a   Wallace, Timothy W ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Bromoketone; 6 endo Trig; Benzo a xanthene; Lauroyl peroxide; Merosesquiterpene; Puupehenone; Radical cyclisation; Sesquiterpene phenol

Indexed keywords

15 OXOPUUPEHENOL; 4 CHROMANONE DERIVATIVE; FREE RADICAL; METAL; NATURAL PRODUCT; PHENOL; PUUPEHENONE; SESQUITERPENE;

ARTICLE; CYCLIZATION; STEREOCHEMISTRY;

EID: 43849110459     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.114     Document Type: Article

References (64)

1. For reviews, see. Blunt J.W., Copp B.R., Hu W.-P., Munro M.H.G., Northcote P.T., and Prinsep M.R. Nat. Prod. Rep. 25 (2008) 35-94
2. Morris J.C., and Phillips A.J. Nat. Prod. Rep. 25 (2008) 95-117
3. Lebar M.D., Heimbegner J.L., and Baker B.J. Nat. Prod. Rep. 24 (2007) 774-797
4. Bowling J.J., Kochanowska A.J., Kasanah N., and Hamann M.T. Exp. Opin. Drug Discovery 2 (2007) 1505-1522
5. Ravi B.N., Perzanowski H.P., Ross R.A., Erdman T.R., Scheuer P.J., Finer J., and Clardy J. Pure Appl. Chem. 51 (1979) 1893-1900
6. Urban S., and Capon R.J. J. Nat. Prod. 59 (1996) 900-901
7. Amade P., Chevelot L., Perzanowski H.P., and Scheuer P.J. Helv. Chim. Acta 66 (1983) 1672-1675
8. Kohmoto S., McConnell O.J., Wright A., Koehn F., Thompson W., Lui M., and Snader K.M. J. Nat. Prod. 50 (1987) 336
9. Hamann M.T., and Scheuer P.J. Tetrahedron Lett. 32 (1991) 5671-5672
10. Hamann M.T., Scheuer P.J., and Kelly-Borges M. J. Org. Chem. 58 (1993) 6565-6569
11. Nasu S.S., Yeung B.K.S., Hamann M.T., Scheuer P.J., Kelly-Borges M., and Goins K. J. Org. Chem. 60 (1995) 7290-7292
12. Bourguet-Kondracki M.-L., Debitus C., and Guyot M. Tetrahedron Lett. 37 (1996) 3861-3864
13. Bourguet-Kondracki M.-L., Lacombe F., and Guyot M. J. Nat. Prod. 62 (1999) 1304-1305
14. Piña I.C., Sanders M.L., and Crews P. J. Nat. Prod. 66 (2003) 2-6
15. Amagata T., Whitman S., Johnson T.A., Stessman C.C., Loo C.P., Lobkovsky E., Clardy J., Crews P., and Holman T.R. J. Nat. Prod. 66 (2003) 230-235
16. Ciavatta M.L., Lopez Gresa M.P., Gavagnin M., Romero V., Melck D., Manzo E., Guo Y.-W., van Soest R., and Cimino G. Tetrahedron 63 (2007) 1380-1384
17. Ueda K., Ogi T., Sato A., Siwu E.R.O., Kita M., and Uemura D. Heterocycles 72 (2007) 655-663
18. Djura P., Stierle D.B., Sullivan B., Faulkner D.J., Arnold E., and Clardy J. J. Org. Chem. 45 (1980) 1435-1441
19. Singh S.B., Zink D.L., Williams M., Polishook J.D., Sanchez M., Silverman K.C., and Lingham R.B. Bioorg. Med. Chem. Lett. 8 (1998) 2071-2076
20. Iwasaki K., Nakatani M., Inoue M., and Katoh T. Tetrahedron 59 (2003) 8763-8773
21. Fenical W., and McConnell O. Experientia 31 (1975) 1004-1005
22. Cimino G., De Stefano S., and Minale L. Experientia 31 (1975) 1117-1118
23. Song F., Fan X., Xu X., Zhao J., Yang Y., and Shi J. J. Nat. Prod. 67 (2004) 1644-1649
24. Kazlauskas R., Murphy P.T., Warren R.G., Wells R.J., and Blount J.F. Aust. J. Chem. 31 (1978) 2685-2697
25. Capon R.J., Groves D.R., Urban S., and Watson R.G. Aust. J. Chem. 46 (1993) 1245-1253
26. Jankam A., Somerville M.J., Hooper J.N.A., Brecknell D.J., Suksamrarn A., and Garson M.J. Tetrahedron 63 (2007) 1577-1582
27. Roll D.M., Manning J.K., and Carter G.T. J. Antibiot. 51 (1998) 635-639
28. Abbanat D.A., Singh M.P., and Greenstein M. J. Antibiot. 51 (1998) 708-714
29. Tsujimori H., Bando M., and Mori K. Eur. J. Org. Chem. (2000) 297-302
30. El Sayed K.A., Bartyzel P., Shen X., Perry T.L., Zjawiony J.K., and Hamann M.T. Tetrahedron 56 (2000) 949-953
31. Barrero A.F., Alvarez-Manzaneda E.J., Chahboun R., Cortés M., and Armstrong V. Tetrahedron 55 (1999) 15181-15208
32. Castro M.E., Gonzalez-Iriarte M., Barrero A.F., Salvador-Tormo N., Munoz-Chapuli R., Medina M.A., and Quesada A.R. Int. J. Cancer 110 (2004) 31-38
33. Douat-Casassus C., Marchand-Geneste N., Diez E., Aznar C., Picard P., Geoffre S., Huet A., Bourguet-Kondracki M.-L., Gervois N., Jotereau F., and Quideau S. Mol. BioSyst. 2 (2006) 240-249
34. Trammell G.L. Tetrahedron Lett. (1978) 1525-1528
35. Barrero A.F., Alvarez-Manzaneda E.J., and Chahboun R. Tetrahedron Lett. 38 (1997) 2325-2328
36. Arjona O., Garranzo M., Mahugo J., Maroto E., Plumet J., and Sáez B. Tetrahedron Lett. 38 (1997) 7249-7252
37. Arjona O., Garranzo M., Mahugo J., Maroto E., Plumet J., and Sáez B. Tetrahedron Lett. 38 (1997) 8605
38. Barrero A.F., Alvarez-Manzaneda E.J., Herrador M.M., Chahboun R., and Galera P. Bioorg. Med. Chem. Lett. 9 (1999) 2325-2328
39. Quideau S., Lebon M., and Lamidey A.-M. Org. Lett. 4 (2002) 3975-3978
40. Armstrong V., Barrero A.F., Alvarez-Manzaneda E.J., Cortés M., and Sepúlveda B. J. Nat. Prod. 66 (2003) 1382-1383
41. Hua D.H., Huang X., Chen Y., Battina S.K., Tamura M., Noh S.K., Koo S.I., Namatame I., Tomoda H., Perchellet E.M., and Perchellet J.-P. J. Org. Chem. 69 (2004) 6065-6078
42. Alvarez-Manzaneda E.J., Chahboun R., Barranco Pérez I., Cabrera E., Alvarez E., and Alvarez-Manzaneda R. Org. Lett. 7 (2005) 1477-1480
43. Villamizar J., Plata F., Canudas N., Tropper E., Fuentes J., and Orcajo A. Synth. Commun. 36 (2006) 311-320
44. Alvarez-Manzaneda E.J., Chahboun R., Cabrera E., Alvarez E., Haidour A., Ramos J.M., Alvarez-Manzaneda R., Hmamouchi M., and Bouanou H. J. Org. Chem. 72 (2007) 3332-3339
45. Quideau S., Pouységu L., and Deffieux D. Synlett (2008) 467-495
46. Maiti S., Sengupta S., Giri C., Achari B., and Banerjee K.K. Tetrahedron Lett. 42 (2001) 2389-2391
47. Ishihara K., Nakamura S., and Yamamoto H. J. Am. Chem. Soc. 121 (1999) 4906-4907
48. Nakamura S., Ishihara K., and Yamamoto H. J. Am. Chem. Soc. 122 (2000) 8131-8140
49. Ishibashi H., Ishihara K., and Yamamoto H. J. Am. Chem. Soc. 126 (2004) 11122-11123
50. Kurdyumov A.V., and Hsung R.P. J. Am. Chem. Soc. 128 (2006) 6272-6273
51. Gansäuer A., Rosales A., and Justicia J. Synlett (2006) 927-929
52. Gansäuer A., Justicia J., Rosales A., Worgull D., Rinker B., Cuerva J.M., and Oltra J.E. Eur. J. Org. Chem. (2006) 4115-4127
53. Crombie B.S., Smith C., Varnavas C.Z., and Wallace T.W. J. Chem. Soc., Perkin Trans. 1 (2001) 206-215
54. Method:. Kabbe H.-J., and Widdig A. Angew. Chem., Int. Ed. Engl. 21 (1982) 247-256
55. f 0.27 (hexane-EtOAc, 3:1).
56. King L.C., and Ostrum G.K. J. Org. Chem. 29 (1964) 3459-3461
57. Procedure for the formation of 23b: A solution of the bromoketone 22b (0.520 g, 1.15 mmol) in dry degassed 1,2-dichloroethane (12 mL) was heated to reflux for 15 min. A solution of dilauroyl peroxide (0.921 g, 2.31 mmol) in dry degassed 1,2-dichloroethane (7 mL) was added dropwise via a pressure-equalising dropping funnel to the refluxing solution over 2.75 h. After the completion of the addition, heating was continued overnight (18.5 h). The reaction mixture was cooled to room temperature and filtered through a pad of basic alumina (5 mm) on top of a pad of silica (20 mm), which was washed successively with EtOAc-hexane (3:1, 80 mL) and dichloromethane (150 mL). The combined filtrate was concentrated in vacuo and purified by flash column chromatography (EtOAc-hexane, 1:9), which gave recovered bromoketone 22b (0.070 g, 13%) and the title compound 23b (0.287 g, 67%, 78% based on recovered 22b) as a white solid.
58. 2) was 0.0907 (all data). Crystallographic data (excluding structure factors) for 23b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 679032. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
59. Ollivier C., Bark T., and Renaud P. Synthesis (2000) 1598-1602
60. Kolly-Kovac T., and Renaud P. Synthesis (2005) 1459-1466
61. Coppa F., Fontana F., Minisci F., Pianese G., Tortoreto P., and Zhao L. Tetrahedron Lett. 33 (1992) 687-690
62. Gagosz F., Moutrille C., and Zard S.Z. Org. Lett. 4 (2002) 2707-2709
63. Alajarín M., Vidal A., and Ortín M.-M. Org. Biomol. Chem. 1 (2003) 4282-4292
64. Fletcher D.A., McMeeking R.F., and Parkin D. J. Chem. Inf. Comput. Sci. 36 (1996) 746-749